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Transferring Fungi to a Deuterium-Enriched Medium Results in Assorted, Conditional Changes in Secondary Metabolite Production

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    Transferring Fungi to a Deuterium-Enriched Medium Results in Assorted, Conditional Changes in Secondary Metabolite Production
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    † ‡ †Natural Product Discovery Group, Institute for Natural Products Applications and Research Technologies, and ‡Department of Chemistry & Biochemistry, Stephenson Life Science Research Center, University of Oklahoma, 101 Stephenson Parkway, Norman, Oklahoma 73019, United States
    § Department of Biochemistry & Molecular Biology, College of Medicine, University of Florida, Gainesville, Florida 32610, United States
    ⊥ NMR Applications Support, Bruker Biospin Corporation, 15 Fortune Drive, Billerica, Massachusetts 01821, United States
    *E-mail: [email protected]. Tel: 405-325-6969. Fax: 405-325-6111.
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2015, 78, 6, 1415–1421
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    https://doi.org/10.1021/acs.jnatprod.5b00337
    Published June 10, 2015
    Copyright © 2015 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    Deuterium is one of the few stable isotopes that have the capacity to significantly alter a compound’s chemical and biological properties. The addition of a single neutron to a protium atom results in the near doubling of its mass, which gives rise to deuterium’s characteristic isotope effects. Since the incorporation of deuterium into organic substrates is known to alter enzyme/protein–substrate interactions, we tested the extent to which deuterium enrichment would modify fungal secondary metabolite production. Several fungal cultures were tested, and in all cases their secondary metabolomes were marked by changes in natural product production. Workup of one Aspergillus sp. grown under deuterium-enrichment conditions resulted in the production of several secondary metabolites not previously detected from the fungus. Bioassay testing revealed that in comparison to the inactive crude fungal extract derived from growing the fungus under non-deuterium-enriched conditions, an extract derived from the same isolate cultured in a deuterium-enriched medium inhibited methicillin-resistant Staphylococcus aureus. Using an assortment of NMR and mass spectrometry experiments, we were able to identify the bacterial inhibitor as an isotope-labeled version of pigmentosin A (6). Five additional isotopically labeled metabolites were also obtained from the fungus including brevianamide F (1), stephacidin A (2), notoamide D (3), notoamide L (4), and notoamide C (5). Given the assorted changes observed in the secondary metabolite profiles of this and other fungi grown in deuterium-enriched environments, as well as the fact that 1 and 3–6 had not been previously observed from the Aspergillus sp. isolate used in this study, we propose that deuterium enrichment might offer an effective method for further expanding a fungus’s chemical diversity potential.

    Copyright © 2015 The American Chemical Society and American Society of Pharmacognosy

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    Supporting Information

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    Secondary metabolome profiles for 16 fungal strains grown in deuterium-enriched and nonenriched media, 1D, 2D NMR spectra and HRESIMS data for compounds 1–6, as well as primary anti-MRSA activity of isolated compounds. The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jnatprod.5b00337.

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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2015, 78, 6, 1415–1421
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jnatprod.5b00337
    Published June 10, 2015
    Copyright © 2015 The American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

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